O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester | 404947-55-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester
• CAS: 404947-55-3
• 化学式: C₃₆H₄₄N₄O₁₁
• 分子量: 708.766
• InChiKey: GACKPYZOCRBTDG-FMAXEKQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  224.84
• 氢给体数：
  6.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以92%的产率得到O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  摘要：

  Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and (2-naphthyl) beta -glycosides, novel muramyl dipeptide derivatives with phenolic aglycons, was reported. The starting N-acetylglucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha -glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta -glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the intended glycopeptides.

  DOI：

  10.1023/a:1012940803366
• 作为产物：
  描述：

  2-萘基 2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧吡喃己糖苷 在 N-羟基丁二酰亚胺 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 10.0h， 生成 O-(2-naphthyl 2-acetamido-2-deoxy-β-D-glucopyranosid-3-yl)-D-lactoyl-L-alanyl-D-isoglutamine benzyl ester
  参考文献：
  名称：

  摘要：

  Synthesis of N-acetylmuramyl-L-alanyl-D-isoglutamine phenyl and (2-naphthyl) beta -glycosides, novel muramyl dipeptide derivatives with phenolic aglycons, was reported. The starting N-acetylglucosamine aryl glycosides were obtained by glycosylation of phenols with peracetylated alpha -glucosaminyl chloride under the conditions of phase-transfer catalysis and used for the synthesis of 4,6-O-isopropylidene-N-acetylmyramic acid aryl beta -glycosides. Condensation of these derivatives with a dipeptide and subsequent deprotection resulted in the intended glycopeptides.

  DOI：

  10.1023/a:1012940803366